1. Field of the Invention
The invention relates to a method of manufacturing a phthalocyanine compound.
2. Discussion of the Background
Phthalocyanine compounds and their analogs are widely employed as dyes and pigments exhibiting high fastness as well as functional coloring materials. The synthesis of phthalocyanine compounds is widely known. One example is a method in which the reaction is conducted in a high-boiling-point alcohol (n-butanol or the like) solvent in the presence of a strong base such as DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) (see Japanese Unexamined Patent Application (KOKAI) Heisei No. 11-269399, or English language family member U.S. Pat. Nos. 5,973,140 and 6,093,832, which are expressly incorporated herein by reference in their entirety). Another is a method employing a metal alkoxide (see Japanese Unexamined Patent Application (KOKAI) Heisei No. 11-209380, which is expressly incorporated herein by reference in its entirety). However, in these methods, the reaction system becomes highly alkaline, precluding the use of matrixes having substituents that tend to decompose under alkaline conditions.
Accordingly, methods of conducting a reaction in the presence of a disilazane such as hexamethyl disilazane with a dimethylformamide solvent (see Japanese Unexamined Patent Application (KOKAI) Nos. 2002-226482 and 2004-26693, which are expressly incorporated herein by reference in their entirety) have been proposed as methods of synthesizing phthalocyanine compounds without employing a strong base. However, problems such as the high cost of disilazanes remain in industrial applications.
In addition, phthalocyanine compounds have large ring structures formed by coordinate bonds between a center metal and four nitrogen atoms surrounding the center metal. Therefore, there is a problem in the synthesis of phthalocyanine compounds in that reactivity varies greatly with the nitrogen affinity of the center metal.